With long days and warm nights, summer weekends are made for exploring. Whether you’re staying local or venturing out, here are a few events worth adding to your calendar.
Join the Hype at Summer Smash
Back for another high-energy weekend, Summer Smash lights up Seatgeek Stadium with three days of nonstop music, food and dancing. This year’s lineup is stacked, with headliners Future, Don Toliver, and Young Thug leading the charge. Expect massive crowds and surprise guest appearances as fans pack in for one of the biggest hip-hop festivals in the Midwest.
Date: June 20-22
Time: Fri 3PM; Sat 1PM; Sun 1PM
Cost: $140+
Location: Seatgeek Stadium, 7000 S Harlem Ave, Bridgeview
More Info: thesummersmash.com
Hunt for Hidden Gems at the Flea Market
Whether you’re a casual browser or a seasoned treasure hunter, this outdoor flea market has something for everyone. Dozens of vendors will be on hand with an eclectic mix of goods; think vintage furniture, handmade crafts, records, art, housewares, and retro fashion. Bring a tote (or two), and come ready to haggle.
Date: June 21
Time: 9AM-3PM
Cost: Free
Location: Joseph C. Vallez Activity Center, 1529 Harlem Ave, Berwyn
More Info: nbpd4fun.org
Honor the Journey at Juneteenth Road to Freedom Commemoration
This Elmhurst-based event combines community reflection with uplifting celebration to honor Juneteenth and its deep historical roots. The program includes a keynote address from Jahmal Cole, founder of My Block, My Hood, My City, plus live jazz by the Evon Sams Combo. Guests can enjoy southern comfort food from Aunt Tina’s Kitchen and explore a silent auction of quilts inspired by the Underground Railroad. It’s a meaningful way to connect, reflect, and support local artists and youth initiatives.
Date: June 22
Time: 10:30AM-12:30PM
Cost: Free
Location: First United Methodist Church, 232 S York St, Elmhurst
More Info: umcelmhurst.org
Celebrate Community at Fiesta Back of the Yards
Now in its 35th year, this neighborhood fest turns Ashland Avenue into a three-block celebration of food, music, carnival rides, and culture. What started as a small community fundraiser has grown into one of the city’s most colorful street festivals, supporting senior services, youth programs, and local arts through BYNC. Expect live performances, dancing, and a true South Side block party feel.
Date: June 20-22
Time: 12PM-10PM
Cost: Free
Location: Ashland Ave from 45th St to 47th St
More Info: bync.org
Love Out Loud at Chicago Pride Fest
Kick off Pride Week at this high-energy street festival in the heart of Northalsted. With three stages of live music, a pet parade, drag shows, and over 150 vendors, the weekend-long party celebrates Chicago’s LGBTQ+ community in full color. Don’t miss performances by the Chicago Gay Men’s Chorus and the all-ages Youth Pride Space.
Date: June 21-22
Time: 11AM-10PM
Cost: $20 Suggested Donation
Location: Halsted St from Addison St to Grace St
More Info: pridechicago.org
Reimagine Waste at RE: Fest
This sustainably-minded street fest highlights the art of reuse, from salvaged home goods to DIY demos. Tour the Rebuilding Exchange warehouse, shop one-of-a-kind creations made from reclaimed materials, and enjoy live music, food trucks, and craft brews in the heart of Bucktown. Proceeds support job training and waste-reduction programs.
Date: June 21
Time: 12PM-8PM
Cost: $10 Suggested Donation
Location: Rebuilding Exchange Chicago., 1740 W Webster Ave
More Info: rebuildingexchange.org
Grow Your Collection at the Chicago Plant Party
Whether you’re a seasoned plant collector or a new plant parent, this leafy pop-up at the Ramova Theatre is a must. Shop greenery, pots, art, and home goods from 30+ local vendors and creators. Expect rare finds, trading opportunities, and plenty of plant puns.
Date: June 22
Time: 12PM-5PM
Cost: $10+
Location: Ramova Theatre, 3520 S Halsted St
More Info: tixr.com
Honor Freedom at the South Side YMCA Juneteenth Celebration
This community-centered Juneteenth event blends history, music, and movement on the South Side. With performances, fitness activities, food, vendors, and family games, the day honors freedom and Black excellence while supporting youth development programs at the Y.
Date: June 21
Time: 12PM-4PM
Cost: Free
Location: South Side YMCA, 6330 S Stony Island Ave
More Info: ymcachicago.org
